


Make Me Feel Good

by MysteriousMidnight



Series: Dear Evan Hansen Smut One Shots [9]
Category: Dear Evan Hansen - Pasek & Paul/Levenson
Genre: Anal Fingering, Blow Jobs, Cunnilingus, F/M, Fluff and Smut, Hand Jobs, One Shot, Oral Sex, Pegging, Smut, Strap-Ons, Vaginal Fingering, conlana, everyone is over 18
Language: English
Status: Completed
Published: 2020-08-09
Updated: 2020-08-09
Packaged: 2021-03-06 07:01:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,505
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25799350
Author URL: https://archiveofourown.org/users/MysteriousMidnight/pseuds/MysteriousMidnight
Summary: Connor wants to try something new with Alana.
Relationships: Alana Beck/Connor Murphy
Series: Dear Evan Hansen Smut One Shots [9]
Series URL: https://archiveofourown.org/series/1825033
Comments: 10
Kudos: 21





	Make Me Feel Good

**Author's Note:**

> Hiiii. More smut. Two days in a row of smut-posting. What have I become? Haha. Anyway, this was a private tumblr request. So... Yeah. Enjoy!

“Hey, Lana?”

Alana glanced up, frowning at the hesitation in Connor’s voice. “Yeah?”

“I-uh... I was thinking about something. But I’m not sure how you’d feel about it.”

“Okay,” Alana said slowly, placing her pen in between the pages of her textbook and settling back against Connor’s headboard.

Connor blew out a breath, standing and walking to his dresser.

“Babe..?” Alana questioned.

“It’s easier to show you,” Connor admitted, pulling something out of his bottom dresser drawer. He stood, hesitating before turning back to Alana. He held whatever it was close to his body as he walked back over and sat on the bed. He took a deep breath before showing it to her.

“Is that.. a strap-on?” Alana asked curiously, holding her hand out for it. Connor nodded, handing it over.

“I was thinking...” he started, licking his lips and shrugging.

“You want me to use this on you?” She asked, quirking a brow in question.

Connor nodded. “I mean, only if you want to. You don’t have to, obviously. You don’t have to do anything you don’t want to-“

She held a hand up. “Connor, stop.” She gave the strap-on a once over before handing it back to him. “We can try it. But not with that. I’ll pick my own strap-on out, thank you very much.”

Connor frowned. “What’s wrong with it?”

“It’s basic,” Alana huffed. “If we’re gonna do this, I’m picking one out that’ll make me feel good, too.”

Connor couldn’t help but grin. “Fair. So you’re really okay with it, though?” He questioned, scooting up beside her and pulling her in for a hug.

“I wouldn’t say yes if I didn’t mean it,” she reminded him, snuggling alongside him and resting her head on his chest.

He kissed the top of her head, rubbing her back. “You’re the best.”

“Oh, trust me. I know,” she said with a smug grin.

~*~*~

**Alana: Are you home alone?**

**Connor: Yeah why?**

**Alana: Coming over**

It had been two weeks since they’d discussed the idea of Alana pegging Connor. He was starting to think she’d changed her mind and just didn’t know how to tell him. But when he opened the front door twenty minutes later, she stood before him with a bag in her hand and a grin on her face.

“How much time do we have?” She asked, making a beeline right for the stairs.

Connor scrambled to lock the door and run after her. “A few hours, probably.”

“Perfect.”

Connor closed his bedroom door behind him, flipping the lock. Alana set her bag on the bed, pulling something out. When she turned around, Connor couldn’t help but gape at her.

The strap-on in her hands was an obnoxious electric blue color. It was big and slightly curved. But what impressed Connor the most was the other end - a second, slightly smaller dildo was attached to it, one clearly meant for the pleasure of the person wearing it.

“It also vibrates on my end,” Alana said, smirking at the look on Connor’s face.

“Fuck,” Connor huffed, stepping closer to Alana and pulling her in for a kiss.

“I told you I’d find one that worked for both of us, it just took a bit of time and some research,” she shrugged.

“As long as you’re happy and _really_ want to do this, that’s all I care about,” he said.

Alana put the box down on the edge of the bed, then turned back to Connor. “As long as _you're_ happy, too,” she reminded him. “It’s not just about me.”

He pulled her close, kissing the tip of her nose. “I’m always happy when I’m with you.”

“Awww, you’re only saying that because you’re about to get laid,” she joked, tugging at his hoodie zipper. When he didn’t stop her, she unzipped it all the way. He shrugged out of it, letting it fall to the floor. He yanked his shirt off next, then pulled Alana back in and nuzzled her neck, kissing and licking his way down to her shoulder, then back up. His fingers slipped under her shirt, hands running along her hips and stomach. She shivered, pressing into his touch.

He made swift work of getting her shirt off, running his hands up her bare arms, brushing them over the top of her breasts, then trailing them back down to her stomach.

“Connor,” she groaned, teasing her fingers along the top of his jeans. He pressed his hips forward, and she took that as her cue to undo his jeans and yank them down, dragging his boxers off along with them.

“Eager?” Connor laughed, stepping out of them and kicking them aside.

Alana grinned up at him, shrugging. “Maybe.”

Connor wrapped his arms around her, loving how warm and soft she was. He planted another kiss on her lips, then rested his forehead against hers. “You smell good,” he murmured, running his fingers under her bra straps. She nodded into him and he unhooked it, gently nudging the straps off one at a time before removing it all together and dropping it into their growing pile of discarded clothes.

He gently pushed her backwards onto the bed, climbing on top of her. He went back to kissing and licking her neck, trailing down her collarbone, her chest, her breasts. He flicked his tongue out at her nipple, before wrapping his mouth around it, licking and sucking.

Alana gasped, pressing up into his mouth. He hummed, making her shiver, before he focused his attention on the side of her breast, intent on sucking a hickey into her skin.

“Shit,” she whimpered, squirming beneath him.

He grinned, pulling away when he was satisfied he’d left a mark. He kissed his way down her stomach, stopping right above her panties and glancing up at her.

“Connor,” she whined, eyes wide with lust.

He planted one more gentle kiss on her stomach before sitting up and pulling her panties off. She shifted her legs as he crawled back between them, kissing her inner thighs, then sucking another hickey into her skin.

She groaned. “You’re determined to leave as many hickeys behind as you can, aren’t you?”

Connor snickered. “Hey, they can all be hidden under clothing. I’m not breaking any rules.”

She rolled her eyes. “You know, you can be such a wise- _fuck_ ,” she cried, bucking her hips when he slipped a finger between her lips, rubbing along her clit. She moaned, letting her knees fall to the side, giving him easier access.

“A wise fuck?” He teased, slipping a finger inside her, making her whimper. “Yeah, I guess I am.”

“Shut up,” she groaned, pressing into his hand. He pumped his finger in and out, then slipped in a second; at the same time, he leaned down and pressed his tongue against her, licking a giant stripe up to her clit, then back down.

She whimpered, fisting her hands in the sheets as he licked and sucked her clit, pumping his fingers mercilessly.

“Connor,” she cried, thighs shaking. He picked up his pace, focusing on her clit until she was writhing and shaking below him. He angled his fingers up, pumping as fast as he could; he knew he’d hit the right spot when she let out a keening whine, body trembling. He didn’t stop until he felt her pulling away, whimpering from the sensitivity. He gave one final lick before pulling his fingers out and resting his head on her leg, grinning up at her.

“Fuck,” she gasped, head thrown back against the pillow. She felt him crawl up her body, pressing a kiss to her lips. She wrapped her arms around him to keep him from moving, deepening the kiss.

“Your turn,” she said, panting. She sat up slowly, body still shaking from her orgasm.

Connor grinned at her. “Need some water first?”

“Please,” she begged, pinching his ass when he turned to walk away. He shot her an amused look before walking out of the room. He was back a few minutes later, water bottle in hand. He plopped down beside her, watching her drink half the water before taking a breath.

She offered him some and he took it gratefully. He took a few sips, then placed it on his nightstand.

“Your turn,” Alana repeated, sitting up and motioning for Connor to take her place.

“You’re hot when you boss me around,” he grinned, settling against the pillows.

“Baby, I’m _always_ hot,” she corrected him. 

He snorted. “Can’t argue with that.”

Alana smirked, straddling his hips, giving him a quick kiss on the lips before moving down to his neck, licking and sucking.

“Heyyyy,” Connor whined. “I didn’t leave marks on _your_ neck.”

“You can hide it with your hair,” she scoffed, nipping him a little harder than usual. He grunted, turning his head to give her better access.

She chuckled. “Oh, don’t want marks but you like being bit, hm?” She licked the bite mark to soothe it, then pressed against his dick, running her clit down his shaft. He shuddered, groaning and trying to grab her hips to keep her in place, but she was too fast; she scooted down, sticking her ass in the air and moving between his legs.

She glanced cheekily up at him, barely giving him a chance to prepare, before he was in her mouth. He moaned, her tongue dancing along the tip, licking at the precum that had leaked out before bobbing back down, pressing her tongue flat against his shaft as she went. It didn’t take long before he was a whimpering, moaning mess.

“Lana,” he gasped, grabbing the hand she had rested on his hip.

She stopped what she was doing, glancing up at him.

“I can’t- I need-“ He panted, struggling to catch his breath.

“Hmm??” She teased, rubbing his stomach gently.

“I’m ready,” he finally said.

She nodded, sitting up. He reached into his drawer and pulled out the bottle of lube. She took it from him and coated her fingers, dropping the bottle to the side. Connor shifted his legs up. Alana shuffled closer to him, resting one hand on his knee and placing the other between his legs; this was the easy part - she’d done this before.

She glanced up at him. “Ready?” When he nodded, she ran her finger along his entrance in teasing circles before pressing in. She pumped her finger slowly at first, then faster, adding a second finger and scissoring them at Connor’s request. He groaned, pressing his hips up into her hand.

“Fuck me,” he choked out, whimpering when her fingers brushed his prostate. “ _Please_.”

She carefully pulled her fingers out, then retrieved the strap on. It took a few tries to get it situated. Once it was in place, she coated her end in lube and pushed it in, moaning and clenching her muscles around it. When she turned around, Connor couldn't help but stare at her, eyes wide with lust.

She grinned, grabbing the vibrator remote and moving back to the bed.

“So,” Alana rubbed his knee. “How, uh...”

Connor frowned, sitting up and grabbing her hand. “You’re shaking.”

“I’m fine,” she insisted. Connor gave her a look. She sighed. “I just... I’m worried I’m going to hurt you.”

Connor shook his head, leaning in to kiss her. “You won’t.”

“Just... promise you’ll tell me if it doesn’t feel right? If I’m hurting you or if you want to stop or-“

“Lana,” he said gently, kissing her forehead and running his hand down her cheek. “I promise. It’ll be fine, okay?”

She nodded, taking a steadying breath. Connor lay back down, staring up at her with trusting eyes. She coated the dildo in lube, then climbed between his legs, lining up with his entrance.

“Ready?” She asked. When he nodded, she slowly eased in. He winced, and she immediately stilled.

“I’m fine,” he assured her. “Just always feels weird at first.”

She frowned, but pushed in a little bit more. Connor groaned, shimmying his hips to encourage her to keep going. When she bottomed out, she paused, giving him a chance to adjust.

“I’m good, you can move,” he said after a minute.

Alana nodded, carefully pulling out, then pushing back in. She went slow at first, still worried she’d hurt him. But the more Connor moaned, and the less resistance she met, the faster she went. He wrapped his legs around her, pulling her close and pressing their lips together. While she was distracted, he reached out and grabbed the vibrator remote, pressing the button to turn on the clit stimulator.

“Fuck,” Alana whined, grinding her hips into Connor, which pressed the vibrator harder against her clit. She whimpered, her thrusts becoming faster, more erratic. One particular thrust had Connor seeing stars.

“Mmmmmm _fuck_ ,” he moaned, as the dildo hit his prostate. Encouraged by his reaction, Alana did her best to hit that same spot, over and over. Connor whimpered, fisting the sheets with one hand and gripping the vibrator control in the other - accidentally hitting the button that increased the intensity of the vibrator.

“ _Shit_ ,” Alana gasped, grinding into the vibrator while still trying to focus on thrusting.

“Close,” Connor groaned. “Lana-“

Alana reached out, grabbing Connor’s dick and pumping. He let out a choked gasp, gripping harder on the vibrator remote. It went up another notch. Alana cried out as her second orgasm of the night rocked through her. A few more erratic thrusts finished Connor off; he moaned long and loud, spilling onto his stomach and Alana’s hand.

Alana collapsed forward, hips twitching. “C-Con- the vibrator,” she whimpered, gasping as a third orgasm washed over her, pain mixing with pleasure. She let out a choked yip, dropping her head onto Connor’s shoulder as he fumbled to turn the vibrator off.

The room was silent, save for their gasping and panting. Finally, Alana gently pulled out. Connor winced at the weird sensation, then opened his arms for Alana to come snuggle. She pulled the strap-on off, then curled into Connor’s arms, legs still shaking.

“That was fucking amazing,” Connor panted, kissing the top of her head.

“Hmmmm,” Alana agreed, burying her face in Connor’s shoulder. She felt him lift her hand up, then felt something wet brush against it. “Wassthat?” She slurred, opening her tired eyes.

“Washcloth,” Connor chuckled. “I had one ready so we wouldn’t have to get up right away.” When he finished cleaning her hand, he moved on to his stomach and dick. He tossed the washcloth into his hamper with perfect accuracy. “Much better,” he sighed pulling her closer and kissing her again.

“Can we do that again?” Alana asked through a yawn. “That was fun.”

“Anytime you want,” Connor assured her. “Take a nap, we’ll shower after, okay?”

“Mhm,” she said, yawning again. “Love you, Con.”

“Love you, too, Lana,” he murmured, rubbing her back as she relaxed in his arms. He tried to stifle a yawn, but failed, giving in to his fatigue and closing his eyes.


End file.
